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Dihydro-pentacene-olefin organic light-emitting material, preparation method and application of dihydro-pentacene-olefin organic light-emitting material

A technology of luminescent materials and pentaphenylene olefins, applied in the preparation of luminescent materials, organic compounds, organic chemistry, etc., can solve the problems of low luminous efficiency and short lifespan, and achieve the effects of high luminous efficiency, improved performance and good application value

Active Publication Date: 2014-07-23
JILIN OPTICAL & ELECTRONICS MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In order to solve the technical problems of low luminous efficiency and short service life of existing blue light organic luminescent materials, the present invention provides a dihydropentacene-based organic luminescent material with high luminous efficiency and long service life; Preparation method and application of pentaphenylene organic luminescent material

Method used

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  • Dihydro-pentacene-olefin organic light-emitting material, preparation method and application of dihydro-pentacene-olefin organic light-emitting material

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1: the synthesis of compound 001

[0034] The specific synthetic route is shown in the following structural formula:

[0035]

[0036](1) Under nitrogen protection system, weigh 110mmol (49.3g) of 3-bromo-N-phenylcarbazole, add 300ml of freshly distilled tetrahydrofuran solution, and add dropwise n-butyllithium 7.19g at -78°C g, reacted for 2 hours, then added dropwise 200ml containing 9-bromo-5,5,14,14-tetramethyl-4a,5,13a,14-dihydropentacene-6,13(4aH,13aH) di Ketone 50mmol (22.4g) tetrahydrofuran solution, after dropwise addition, under the condition of nitrogen protection, react at room temperature for 8 hours, add 100ml of 1M dilute hydrochloric acid, extract 3 times with 100ml of ether, separate liquid, concentrate, use dichloromethane: Petroleum ether=1:3 recrystallized to obtain 41.2g of off-white intermediate N-phenyl-3-carbazolyldihydropentacene alcohol derivatives.

[0037] (2) Take N-phenyl-3-carbazolyldihydropentacene alcohol derivatives, add...

Embodiment 2

[0040] Embodiment 2: the synthesis of compound 004

[0041] The specific synthetic route is shown in the following structural formula:

[0042]

[0043] (1) Under a nitrogen protection system, weigh 110mmol (28.5g) of 3-bromo-phenanthrolinyl, add 300ml of freshly steamed tetrahydrofuran solution, and add 7.19g of n-butyllithium dropwise at -78°C to react 6 hour, then dropwise added 200ml of 9-bromo-5,5,14,14-tetramethyl-4a,5,13a,14-dihydropentacene-6,13(4aH,13aH)dione 50mmol ( 22.4g) of tetrahydrofuran solution, after the dropwise addition, under the condition of nitrogen protection, react at room temperature for 9 hours, add 100ml of 1M dilute hydrochloric acid, extract 3 times with 100ml of ether, separate liquid, concentrate, use dichloromethane:petroleum ether= 1:3 recrystallization to obtain 39.4g off-white intermediate 3-phenanthrolinyldihydropentacene alcohol derivatives.

[0044] (2) Take 3-phenanthrolinyldihydropentacene alcohol derivatives, add them to 300ml of ...

Embodiment 3

[0047] Embodiment 3: the synthesis of compound 007

[0048] The specific synthetic route is shown in the following structural formula:

[0049]

[0050] (1) Under the condition of nitrogen protection, weigh 110mmol (35.5g) of 4-bromo-triarylamino group, add 300ml of freshly steamed tetrahydrofuran solution, and add 7.19g of n-butyllithium dropwise at -78°C to react 4 hours, then dropwise added 200ml containing 9-bromo-5,5,14,14-tetramethyl-4a,5,13a,14-dihydropentacene-6,13(4aH,13aH) dione 50mmol ( 22.4g) of tetrahydrofuran solution, after the dropwise addition, under the condition of nitrogen protection, react at room temperature for 9 hours, add 100ml of 1M dilute hydrochloric acid, extract 3 times with 100ml of ether, separate liquid, concentrate, use dichloromethane:petroleum ether= 1:3 recrystallization to obtain 41.6 g of off-white intermediate triarylaminodihydropentacene alcohol derivatives.

[0051] (2) Take triarylaminodihydropentacene alcohol derivatives, add th...

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Abstract

The invention relates to a dihydro-pentacene-olefin organic light-emitting material, a preparation method and an application of the dihydro-pentacene-olefin organic light-emitting material, and solves technical problems of low luminous efficiency and short service life of the existing blue organic light-emitting material. The material is based on a dihydro-pentacene compound which has a larger plane structure and a larger conjugated system in comparison with anthracene derivatives; and methyl and aryl substituent groups of other condensed rings are adopted, so that the performance of the dihydro-pentacene-olefin organic light-emitting material is improved well and the dihydro-pentacene-olefin organic light-emitting material is a novel high-performance electroluminescent material. The invention also provides the preparation method of the dihydro-pentacene-olefin organic light-emitting material. According to the preparation method, reaction conditions are optimized, so that a reaction solvent is changed to be an ordinary solvent, so that the operation is convenient, the purification is easy, the yield is greatly increased and the cost is lowered. The dihydro-pentacene-olefin organic light-emitting material provided by the invention is applied to the organic electroluminescent material and has high luminous efficiency.

Description

technical field [0001] The invention belongs to the field of organic photoelectric materials, and in particular relates to a dihydropentacene-based organic light-emitting material and its preparation method and application. Background technique [0002] As a flat panel display technology, organic electroluminescent devices have many advantages such as self-illumination, high brightness, wide viewing angle, ultra-thin, low energy consumption, fast response, rollable, full-color luminescence, etc., and have been favored by people. focus on. The performance of organic electroluminescent devices can be significantly improved by adopting appropriate device structure, device fabrication technology and organic materials. For example, in terms of full-color display, high-efficiency and stable green organic electroluminescent devices have reached the practical level. Compared with green organic electroluminescent devices, blue organic electroluminescent devices cannot fully meet the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/86C07D471/04C07C211/54C07C209/68C07C217/80C07C13/62C07C43/215C07C29/32C07C43/23C09K11/06H01L51/54
Inventor 马晓宇王辉李文军
Owner JILIN OPTICAL & ELECTRONICS MATERIALS
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